Methyl iodide → 2-Bromo-3-methoxy-6-methylpyridine

HRID 1765409Notes

Reaction equation

HRID 1765409 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[C:10](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[Br:1][C:2]1[C:7]([O:8][CH3:10])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 119591012-Bromo-6-methylpyridin-3-ol

Product 1

HCID 109655632-Bromo-3-methoxy-6-methylpyridineYield 88.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 2-bromo-3-hydroxy-6-methyl-pyridine (7.89 g, 42.0 mmol), potassium carbonate (11.60 g, 83.9 mmol) and iodomethane (8.93 g, 62.9 mmol, 3.92 mL) in acetone (100 mL) was heated under reflux overnight. The mixture was filtered, evaporated and purified on silica gel (hexane:ethyl acetate, 95:5 to 9:1) to give the desired product as a white solid (7.49 g, 88.3%). 1H NMR (500 MHz, CDCl3): δ 2.46 (s, 3 H), 3.87 (s, 3 H), 7.04 (s, 2 H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. filtrationThe mixture was filtered
  4. customevaporated
  5. custompurified on silica gel (hexane:ethyl acetate, 95:5 to 9:1)

Sources & evidence

ORD record
ord-458b7aab054546afa5e1a3e656df4eaa
Source dataset
uspto-grants-2007_06
Patent number
US07226940B2

Reaction notes

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